[go: up one dir, main page]

US3236624A - Method for selectively killing undesired plants - Google Patents

Method for selectively killing undesired plants Download PDF

Info

Publication number
US3236624A
US3236624A US235531A US23553162A US3236624A US 3236624 A US3236624 A US 3236624A US 235531 A US235531 A US 235531A US 23553162 A US23553162 A US 23553162A US 3236624 A US3236624 A US 3236624A
Authority
US
United States
Prior art keywords
plants
undesired plants
chlorophenyl
urea
parts
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US235531A
Inventor
Martin Henry
Aebi Hans
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Schweiz AG
Original Assignee
Ciba AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from CH7720859A external-priority patent/CH384283A/en
Application filed by Ciba AG filed Critical Ciba AG
Application granted granted Critical
Publication of US3236624A publication Critical patent/US3236624A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04—Derivatives of thiourea
    • C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups

Definitions

  • the present invention is based on the unexpected observation that N-phenyl-N-alkyl-ureas which contain a trifluoromethyl group and are halogen-substituted in the phenyl nucleus and correspond to the general formula in which R represents a lower alkyl group, R represents a hydrogen atom or a lower alykl group and X represents an oxygen or sulfur atom, possess selective herbicidal action.
  • the present invention therefore relates to a method for selectively combating undesired plants growing beneath crop plants, wherein there is applied to the area in which the herbicidal effect is desired, in an amount which is sufiicient to kill the undesired plants a compound of the general Formula I set forth above.
  • the compounds of the above general formulae can be made by the application of known general methods, all the customary methods for making derivatives of urea or thiourea being generally suitable. There are indicated below a few methods, but these are not to be regarded as exhaustive; (the halogen-substituted phenyl radical containing a trifiuoromethyl group is denoted by the symbol Ar, and R and R in the formulae below represents methyl groups) CH3 /CH3 Ar-NH 00N
  • isocyanate there may be used a substance that forms isocyanate or splits otf isocyanate
  • the active substance may be used in emulsified, dispersed or dissolved form or in the form of dusting preparations.
  • the compounds may be used alone or together with other selective herbicidal substances, or with borax or other inorganic salts, such as abraum salts, calcium cyanamide, urea or other fertilizers, or pest combating agents, for example, chlorinated hydrocarbons or phosphoric acid esters.
  • borax or other inorganic salts such as abraum salts, calcium cyanamide, urea or other fertilizers, or pest combating agents, for example, chlorinated hydrocarbons or phosphoric acid esters.
  • organic solvents preferably boiling above C.
  • mineral oil fractions of high to medium boiling range such as diesel oil or kerosene, or coal tar oils or oils of vegetable or animal origin and also hydrocarbons, such as alkylated naphthalenes, tetrahydronaphthalene, if desired, with the use of mixt-ures of xylenes, cyclohexanols, ketones, also chlorinated hydrocarbons, such as tetrachlorethane, trichlorethylene or trior tetrachloro-benzenes.
  • mineral oil fractions of high to medium boiling range such as diesel oil or kerosene, or coal tar oils or oils of vegetable or animal origin
  • hydrocarbons such as alkylated naphthalenes, tetrahydronaphthalene, if desired, with the use of mixt-ures of xylenes, cyclohexanols, ketones, also chlorinated hydrocarbons, such
  • Aqueous preparations for direct use can be prepared by mixing water with an emulsion concentrate, paste or wettable powder containing the active substance.
  • emulsifying or dispersing agents there may be used non ionic substances, for example, condensation products of aliphatic alcohols, amines or carboxylic acids having long-chain hydrocarbon radicals containing about 10 to 30 carbon atoms, with ethylene oxide, such as the condensation product of octadecyl alcohol with 25 to 30 mols of ethylene oxide, or a condensation product of commercial oleylamine with 15 mols of ethylene oxide, or a condensation product of dodecyl-mercaptan with 12 mols of ethylene oxide.
  • anion-active emulsifying agents that may be used, there may be mentioned the sodium salt of dodecyl alcohol sulfuric acid ester, the sodium salt of dodecylbenzene-sulfonic acid, the potassium or triethanolamine salt of oleic acid or of abietic acid, or mixtures of these acids, or the sodium salt of a petroleum sulfonic acid.
  • cation-active emulsifying agents there may be mentioned quaternary ammonium compounds, such as eetyl-pyridinium bromide or dihydroxybenzyldodecyl-ammonium chloride.
  • talcum for making dusting or scattering preparations there may be used as carriers talcum, kaolin, bentonite, calcium carbonate or calcium phosphate, or carbon, cork meal or Wood meal, and other materials of vegetable origin. It is very advantageous to make up the preparations in a granular form.
  • the various preparations can be rendered more suitable for the methods in which they are to be used by the known addition or substances which improve the dispersion, adhesiveness, resistance to rain or penetration capacity of the compositions.
  • fatty acids for example, alginates or the like.
  • the herbicidal preparations of this invention are suitable e.g. for the selective destruction of weeds under crop plants.
  • weeds is used in this connection to include undesired plants, for example plants previously planted on the area which is to be treated.
  • EXAMPLE 1 443 grams of 3-trifiuoromethyl-4-ehlorophenyl isocyanate, dissolved in 200 cc. of acetone, are added slowly to 270 cc. of an aqueous dimethylamine solution of 40% strength in 1500 cc. of water while stirring vigorously. With a slight increase in temperature to 40 C., the condensation to give N 3-trifiuoromethyl 4-chlorophenyl- N'tN-dimethyl urea takes place, this being immediately precipitated in a technically pure state. After stirring for six hours, a little water is added and the urea is filtered off with suction, washed with water and a little dilute acetic acid and dried in vacuo at 60 C. Crude yield: 516.0 grams; melting point: 137 to 138 C. A test sample recrystallized from alcohol shows a melting point of 139 to 140 C.
  • N-3-trifiuoromethyl- 4-chlorophenyl-N-methyl-N-n-butyl urea appears as oil which boils at 0.01 mm. between 170 and 180 C. Solidification point: 54.5 to 55.5 C.
  • 3-trifluoromethyl-4-chlorophenyl isocyanate gives under the same conditions N-3-trifluoromethyl-4- chlorophenyl-N'-methyl urea having a melting point of 130 to 131 C.
  • EXAMPLE 4 20 parts of N-3-trifluoromethyl-4-chlorophenyl-N':N'- dimethyl urea and parts of talc are ground very finely in a ball mill. The mixture so obtained is used as a dusting agent.
  • EXAMPLE 5 20 parts of N-3-trifluoromethyl-4-chloropheny1-N'2N- dimethyl urea are dissolved in a mixture of 48 parts of diacetone alcohol, 16.5 parts of xylene and 16 parts of a condensation product of ethylene oxide with higher fatty acids, for example the condensation product of soyabean fatty acid and 30 mols of ethylene oxide.
  • This concentrate may be diluted with water to give emulsions of any desired concentration. It is also possible to employ N-3-trifluoromethyl-4-chlorophenyl-N-methyl urea.
  • EXAMPLE 6 80 parts of N-3-trifluoromethyl-4-chlorophenyl-N':N'- dimethyl urea or equal parts of N-3-trifiuoromethyl-4- chlorophenyl-N-methyl urea are mixed with 4 parts of a Wetting agent, for example the sodium salt of butylnaphthalenesulfonic acid, 1 to 3 parts of a protective colloid, for example sul'fite waste liquor, and 15 parts of solid inert carrier such a kaolin, chalk or kieselguhr and thereupon finely ground.
  • a Wetting agent for example the sodium salt of butylnaphthalenesulfonic acid
  • a protective colloid for example sul'fite waste liquor
  • solid inert carrier such as kaolin, chalk or kieselguhr and thereupon finely ground.
  • the wettable powder obtained may be mixed with Water before used and gives a suspension which is ready for use.
  • EXAMPLE 7 15 parts of N-3-trifiuoromethyl-6-chlorophenyl-N'-:N- dimethyl urea are dissolved in parts of coal-tar oil, diesel oil or spindle oil.
  • EXAMPLE 8 To 10 grams of compounds (a), (b), (c) and (d) there are added separately in each case 2 grams of waste sulfite pulp liquor and cc. of water and the mixture is thereafter subjected to intensive grinding, whereby'finely divided, stable dispersions are obtained (c) Cl C H: NHC O-N l 0 Fa (ll-O-NH-O SN CH: C Fa EXAMPLE 9 80 parts of compounds (at) and (b) are mixed with 16 parts of kaolin and 4 parts of an emulsifier supplied by Ninol Inc., Chicago, under the trademark Toximul MP and finely ground. The mixtures can be used as spraying powders.
  • EXAMPLE 10 Flower pots are filled with earth in a greenhouse and sown with seeds of the weeds and cultivated plants named hereunder: Zea mays, Avena sativa, Setaria italica, Dactylis glomerata, Sinapis alba, Lepidium sativum, Calendula chrysantha.
  • the plants are sprayed with a spraying liquid obtained from the dispersions (a) to (d) according to Example 8, the quantity of each active substance employed corresponding to 10 kg. per hectare. As the absorption of the active substance also takes place through the leaves, the treated plants, with the exception of Zea mays, which was practically not inhibited, already died off completely or almost completely after 14 days.
  • kaolin bolus alba
  • compositions (a), (b), (c) and (d) Pre-emergency Flower pots were filled with earth in a greenhouse and sown with seeds of the plants named below in Table I.
  • the earth was watered and treated on the day after sowing with an aqueous dispersion obtained by diluting the composition (41) set forth above, with water.
  • the quantity of the active substance employed corresponded to 3 kg./hectare.
  • the concentration of the active substance in each spraying liquor was 0.60%.
  • the results of the treatment were examined 3 weeks later.
  • composition (b) or (c) Post-emergence Flowerpots were filled with earth in a greenhouse and sown with seeds of the plants named below in Table II.
  • the earth in the flower pots was treated about 2 weeks after sowing when the plants had developed 2 to 4 true leaves, with an aqueous dispersion obtained by diluting each of the compositions (a) and (d) set forth above with Water.
  • the quantity of the active substances employed corresponded in the case of the compound (a) to 2 kg./hectare, in the case of the compound (d) to 6 kg./hectare.
  • the concentration of the active substance in each spraying liquor was 0.60% by weight.
  • the results of the treatment were examined 3 weeks after the treatment.
  • compositions used in the claimed method practically do not inhibit the growth of important useful plants such as beans, peas, carrots, flax, and on the other hand, kill or damage heavily the grasses Alopecurus, Poa and Dactylis which of course, are highly undesired in cultures of the aforesaid useful plants.
  • compositions (a) to (d) set forth above under (A) are applied at a rate of 3 to 10 kg. of active substance/hectare to an asparagus field all the weeds, growing said field are completely or almost completely destroyed. On the other hand no damage can be observed in case of the asparagus.
  • the following weeds have been killed: Euphorbia hclioscopia, Senecio vulgaris, Sonchus asper, Stellaria media, Chenopodium album, Veronica species, T hlaspi arvense, Poa mmua.
  • a method for selectively combating undesired plants growing beneath maize wherein there is applied to the area in which the herbicidal effect is desired, in an amount which is sufficient to kill the undesired plants a compound of the formula CFa X 7 area in which the herbicidal effect is desired, in an amount which is sufficient to kill the undesired plants a compound of the formula in which R represents lower alkyl, R represents a member selected from the group consisting of hydrogen and lower alkyl, and X represents a member selected from the group consisting of oxygen and sulfur.
  • N-3-trifiuoromethyl-4-chlorophenyl-N',N'-dimethyl urea is applied at the rate of 2 to 6 kilograms per hectare.
  • a method for selectively combating undesired plants growing beneath peas wherein there is applied to the area in which the herbicidal effect is desired, in an amount which is sufficient to kill the undesired plants a compound of the formula in which R represents lower alkyl, R represents a member selected from the group consisting of hydrogen and lower alkyl, and X represents a member selected from the group consisting of oxygen and sulfur.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

United States Patent 3,236,624 METHOD FOR SELECTIVELY KILLING UNDESIRED PLANTS Henry Martin, Basel, and Hans Aebi, Riehen, Switzerland,
assignors t0 Ciba Limited, Basel, Switzerland, a company of Switzerland No Drawing. Filed Nov. 5, 1962, Ser. No. 235,531 Claims priority, application Switzerland, Aug. 21, 1959, 77,208/59 The portion of the term of the patent subsequent to May 26, 1981, has been disclaimed 8 Claims. (Cl. 712.6)
This is a continuation in part of our copending application Serial No. 46,346, filed August 1, 1960, now US. Patent No. 3,134,665.
The present invention is based on the unexpected observation that N-phenyl-N-alkyl-ureas which contain a trifluoromethyl group and are halogen-substituted in the phenyl nucleus and correspond to the general formula in which R represents a lower alkyl group, R represents a hydrogen atom or a lower alykl group and X represents an oxygen or sulfur atom, possess selective herbicidal action. The present invention therefore relates to a method for selectively combating undesired plants growing beneath crop plants, wherein there is applied to the area in which the herbicidal effect is desired, in an amount which is sufiicient to kill the undesired plants a compound of the general Formula I set forth above.
Abel et al. described in Chemistry and Industry (1957) at page 1106 the inhibition of the so-called Hill-reaction, which is used to measure the photolysis of water in the presence of isolated chloroplasts, by N-4- and N-S-trifluormethyl-phenyl-N,N'-dimethyl urea. From this inhibiting action the useful selective herbicidal properties of the claimed new compounds could of course, not be expected.
Among the compounds of the above Formula I there are especially useful those of the general formula in which X, R and R have the meanings given above. Among the compounds of the latter formula there are preferred those in which R represents a methyl or ethyl group and R a hydrogen atom, or methyl or ethyl group.
The compounds of the above general formulae can be made by the application of known general methods, all the customary methods for making derivatives of urea or thiourea being generally suitable. There are indicated below a few methods, but these are not to be regarded as exhaustive; (the halogen-substituted phenyl radical containing a trifiuoromethyl group is denoted by the symbol Ar, and R and R in the formulae below represents methyl groups) CH3 /CH3 Ar-NH 00N Instead of isocyanate, there may be used a substance that forms isocyanate or splits otf isocyanate For use the compounds of the general Formula I are advantageously made up into preparations, which are also included in the invention. The active substance may be used in emulsified, dispersed or dissolved form or in the form of dusting preparations.
The compounds may be used alone or together with other selective herbicidal substances, or with borax or other inorganic salts, such as abraum salts, calcium cyanamide, urea or other fertilizers, or pest combating agents, for example, chlorinated hydrocarbons or phosphoric acid esters.
For making solutions to be used for direct spraying there may be used organic solvents, preferably boiling above C., for example, mineral oil fractions of high to medium boiling range, such a diesel oil or kerosene, or coal tar oils or oils of vegetable or animal origin and also hydrocarbons, such as alkylated naphthalenes, tetrahydronaphthalene, if desired, with the use of mixt-ures of xylenes, cyclohexanols, ketones, also chlorinated hydrocarbons, such as tetrachlorethane, trichlorethylene or trior tetrachloro-benzenes.
Aqueous preparations for direct use can be prepared by mixing water with an emulsion concentrate, paste or wettable powder containing the active substance. As emulsifying or dispersing agents there may be used non ionic substances, for example, condensation products of aliphatic alcohols, amines or carboxylic acids having long-chain hydrocarbon radicals containing about 10 to 30 carbon atoms, with ethylene oxide, such as the condensation product of octadecyl alcohol with 25 to 30 mols of ethylene oxide, or a condensation product of commercial oleylamine with 15 mols of ethylene oxide, or a condensation product of dodecyl-mercaptan with 12 mols of ethylene oxide. Among anion-active emulsifying agents, that may be used, there may be mentioned the sodium salt of dodecyl alcohol sulfuric acid ester, the sodium salt of dodecylbenzene-sulfonic acid, the potassium or triethanolamine salt of oleic acid or of abietic acid, or mixtures of these acids, or the sodium salt of a petroleum sulfonic acid. As cation-active emulsifying agents there may be mentioned quaternary ammonium compounds, such as eetyl-pyridinium bromide or dihydroxybenzyldodecyl-ammonium chloride. For making dusting or scattering preparations there may be used as carriers talcum, kaolin, bentonite, calcium carbonate or calcium phosphate, or carbon, cork meal or Wood meal, and other materials of vegetable origin. It is very advantageous to make up the preparations in a granular form. The various preparations can be rendered more suitable for the methods in which they are to be used by the known addition or substances which improve the dispersion, adhesiveness, resistance to rain or penetration capacity of the compositions. As such substances there may be mentioned fatty acids, resins, glue, casein or, for example, alginates or the like.
The herbicidal preparations of this invention are suitable e.g. for the selective destruction of weeds under crop plants. The term weeds is used in this connection to include undesired plants, for example plants previously planted on the area which is to be treated.
The following examples illustrate the invention:
EXAMPLE 1 443 grams of 3-trifiuoromethyl-4-ehlorophenyl isocyanate, dissolved in 200 cc. of acetone, are added slowly to 270 cc. of an aqueous dimethylamine solution of 40% strength in 1500 cc. of water while stirring vigorously. With a slight increase in temperature to 40 C., the condensation to give N 3-trifiuoromethyl 4-chlorophenyl- N'tN-dimethyl urea takes place, this being immediately precipitated in a technically pure state. After stirring for six hours, a little water is added and the urea is filtered off with suction, washed with water and a little dilute acetic acid and dried in vacuo at 60 C. Crude yield: 516.0 grams; melting point: 137 to 138 C. A test sample recrystallized from alcohol shows a melting point of 139 to 140 C.
C H ON ClF I CalculatedN, 10.5%; CI, 13.3% FoundN, 10.18%; Cl, 13.03%.
Prepared under the same conditions, N-3-trifiuoromethyl- 4-chlorophenyl-N-methyl-N-n-butyl urea appears as oil which boils at 0.01 mm. between 170 and 180 C. Solidification point: 54.5 to 55.5 C. Condensed with monomethylamine, 3-trifluoromethyl-4-chlorophenyl isocyanate gives under the same conditions N-3-trifluoromethyl-4- chlorophenyl-N'-methyl urea having a melting point of 130 to 131 C.
C9H9ON2C1F3 Calculated-N, 11.09%; Cl, 14.04% FoundN, 11.18%; Cl, 13.65%.
EXMPLE 2 In the same way as the described in Examples 1 and 2, the following urea derivatives can also be prepared.
N-3-trifluoromethyl-4-chlorophenyl-N :N-diethy1 urea melting point 116 to 117 C. C H
1 CH3 CF:
N-S-trlfluoromethyl-4-cl1lorophenyl-N-isopropyl urea melting point 154 to 155 C.
l CFa EXAMPLE 3 210 grams of 3-t1ifluoromethyl-4-chlorophenyl isothiocyanate (distilled under 11 mm. of pressure at 119-120 C.; under 0.04 mm. at 70-73 0), dissolved in 200 cc. of acetone, are added drop by drop to 1 liter of water and 130 cc. of aqueous dimethylamine solution of 40% strength while stirring. N-3-trifiuoromethyl-4-chlorophenyl-N:N-dimethyl thiourea is precipitated in the process. This is filtered off, washed with Water and a little dilute acetic acid and dried in vacuo at 60 C. The crude yield is 244 grams. The crude condensation product has a melting point of 157158 C. Recrystallized from alcohol, the compound melts at 159-160 C. C H N ClF S:
CalculatedN, 9.91%; Cl 12.54; S, 11.35% Found-N, 10.12%; Cl 12.60%; S, 11.45%.
EXAMPLE 4 20 parts of N-3-trifluoromethyl-4-chlorophenyl-N':N'- dimethyl urea and parts of talc are ground very finely in a ball mill. The mixture so obtained is used as a dusting agent.
EXAMPLE 5 20 parts of N-3-trifluoromethyl-4-chloropheny1-N'2N- dimethyl urea are dissolved in a mixture of 48 parts of diacetone alcohol, 16.5 parts of xylene and 16 parts of a condensation product of ethylene oxide with higher fatty acids, for example the condensation product of soyabean fatty acid and 30 mols of ethylene oxide. This concentrate may be diluted with water to give emulsions of any desired concentration. It is also possible to employ N-3-trifluoromethyl-4-chlorophenyl-N-methyl urea.
EXAMPLE 6 80 parts of N-3-trifluoromethyl-4-chlorophenyl-N':N'- dimethyl urea or equal parts of N-3-trifiuoromethyl-4- chlorophenyl-N-methyl urea are mixed with 4 parts of a Wetting agent, for example the sodium salt of butylnaphthalenesulfonic acid, 1 to 3 parts of a protective colloid, for example sul'fite waste liquor, and 15 parts of solid inert carrier such a kaolin, chalk or kieselguhr and thereupon finely ground. The wettable powder obtained may be mixed with Water before used and gives a suspension which is ready for use.
EXAMPLE 7 15 parts of N-3-trifiuoromethyl-6-chlorophenyl-N'-:N- dimethyl urea are dissolved in parts of coal-tar oil, diesel oil or spindle oil.
EXAMPLE 8 To 10 grams of compounds (a), (b), (c) and (d) there are added separately in each case 2 grams of waste sulfite pulp liquor and cc. of water and the mixture is thereafter subjected to intensive grinding, whereby'finely divided, stable dispersions are obtained (c) Cl C H: NHC O-N l 0 Fa (ll-O-NH-O SN CH: C Fa EXAMPLE 9 80 parts of compounds (at) and (b) are mixed with 16 parts of kaolin and 4 parts of an emulsifier supplied by Ninol Inc., Chicago, under the trademark Toximul MP and finely ground. The mixtures can be used as spraying powders.
EXAMPLE 10 Flower pots are filled with earth in a greenhouse and sown with seeds of the weeds and cultivated plants named hereunder: Zea mays, Avena sativa, Setaria italica, Dactylis glomerata, Sinapis alba, Lepidium sativum, Calendula chrysantha.
The plants are sprayed with a spraying liquid obtained from the dispersions (a) to (d) according to Example 8, the quantity of each active substance employed corresponding to 10 kg. per hectare. As the absorption of the active substance also takes place through the leaves, the treated plants, with the exception of Zea mays, which was practically not inhibited, already died off completely or almost completely after 14 days.
EXAMPLE 11 (A) From each of the compounds set forth above in Example 8 under (a) to (d) there was made a wettable powder of the following composition:
20% by weight of active substance.
25% by weight of finely divided SiO 3.5% by weight of a condensation product of 1 molecular proportion of dodecyl mercaptan and 12 molecular proportions of ethylene oxide.
1.5% by weight of a condensation product of 1 molecular proportion of p-nonyl phenol and 9 molecular proportions of ethylene oxide, and
50% by weight of kaolin (bolus alba) by mixing and grinding.
The following tests were carried out with so-obtained compositions (a), (b), (c) and (d) Pre-emergency Flower pots were filled with earth in a greenhouse and sown with seeds of the plants named below in Table I. The earth was watered and treated on the day after sowing with an aqueous dispersion obtained by diluting the composition (41) set forth above, with water. The quantity of the active substance employed corresponded to 3 kg./hectare. The concentration of the active substance in each spraying liquor was 0.60%. The results of the treatment were examined 3 weeks later.
TABLE I Test plants Composition(d) Daucus carota Linmn usitattsszmum Not inhibited. Only slightly inhibited.
Completely killed.
Do. Do.
Similar results are obtained with composition (b) or (c). Post-emergence Flowerpots were filled with earth in a greenhouse and sown with seeds of the plants named below in Table II. The earth in the flower pots was treated about 2 weeks after sowing when the plants had developed 2 to 4 true leaves, with an aqueous dispersion obtained by diluting each of the compositions (a) and (d) set forth above with Water. The quantity of the active substances employed corresponded in the case of the compound (a) to 2 kg./hectare, in the case of the compound (d) to 6 kg./hectare. The concentration of the active substance in each spraying liquor was 0.60% by weight. The results of the treatment were examined 3 weeks after the treatment.
The results are shown in the following Table II.
TAB LE II Test plants Composition(a) Composition (d) Pisum satiuum Practically no damage. Daucus carota "do Alopecurus pratensz's Heavy damage,
cannot recover.
Poa trivialis do Dactylis glomcrata Completely killed Completely killed.
Do. Do.
From the results set forth above in Tables I and II it can be seen that the compositions used in the claimed method practically do not inhibit the growth of important useful plants such as beans, peas, carrots, flax, and on the other hand, kill or damage heavily the grasses Alopecurus, Poa and Dactylis which of course, are highly undesired in cultures of the aforesaid useful plants.
(B) When the compositions (a) to (d) set forth above under (A) are applied at a rate of 3 to 10 kg. of active substance/hectare to an asparagus field all the weeds, growing said field are completely or almost completely destroyed. On the other hand no damage can be observed in case of the asparagus. The following weeds have been killed: Euphorbia hclioscopia, Senecio vulgaris, Sonchus asper, Stellaria media, Chenopodium album, Veronica species, T hlaspi arvense, Poa mmua.
What is claimed is:
1. A method for selectively combating undesired plants growing beneath maize wherein there is applied to the area in which the herbicidal effect is desired, in an amount which is sufficient to kill the undesired plants a compound of the formula CFa X 7 area in which the herbicidal effect is desired, in an amount which is sufficient to kill the undesired plants a compound of the formula in which R represents lower alkyl, R represents a member selected from the group consisting of hydrogen and lower alkyl, and X represents a member selected from the group consisting of oxygen and sulfur.
4. A method as claimed in claim 3 wherein N-3-trifiuoromethyl-4-chlorophenyl-N',N'-dimethyl urea is applied at the rate of 2 to 6 kilograms per hectare.
5. A method for selectively combating undesired plants growing beneath peas wherein there is applied to the area in which the herbicidal effect is desired, in an amount which is sufficient to kill the undesired plants a compound of the formula in which R represents lower alkyl, R represents a member selected from the group consisting of hydrogen and lower alkyl, and X represents a member selected from the group consisting of oxygen and sulfur.
6. A method as claimed in claim 5, wherein N-3-trifluoromethyl-4-chlorophenyl-N,N'-dimethyl urea is applied at the rate of 2 to 6 kilograms per hectare.
7. A method for selectively combating undesired plants growing beneath asparagus wherein there is applied to the area in which the herbicidal effect is desired, in an amount which is sufficient to kill the undesired plants a compound of the formula References Cited by the Examiner UNITED STATES PATENTS 'l0/i1953 Todd 712.6
OTHER REFERENCES Abel, Chemistry and Industry, 1957, pages 1106 to 1112.
Crafts, The Chemistry and Mode of Action of Herbicides, Interscience Publishers, New York, 1961, pages 77 to 80 and 117 to 120.
LEWIS GOTTS, Primary Examiner.
JULIAN S. LEVITT, Examiner.
JAMES O. THOMAS, Assistant Examiner.

Claims (1)

1. A METHOD FOR SELECTIVELY COMBATING UNDESIRED PLANTS GROWING BENEATH MAIZE WHEREIN THERE IS APPLIED TO THE AREA IN WHICH THE HERBICIDAL EFFECT IS DESIRED, IN AN AMOUNT WHICH IS SUFFICIENT TO KILL THE UNDERSIRED PLANTS A COMPOUND OF THE FORMULA
US235531A 1959-08-21 1962-11-05 Method for selectively killing undesired plants Expired - Lifetime US3236624A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH7720859A CH384283A (en) 1959-08-21 1959-08-21 Herbicides
CH7775459A CH384284A (en) 1959-08-21 1959-09-03 Herbicides

Publications (1)

Publication Number Publication Date
US3236624A true US3236624A (en) 1966-02-22

Family

ID=25738330

Family Applications (2)

Application Number Title Priority Date Filing Date
US46346A Expired - Lifetime US3177249A (en) 1959-08-21 1960-08-01 N-trifluoromethylphenyl urea
US235531A Expired - Lifetime US3236624A (en) 1959-08-21 1962-11-05 Method for selectively killing undesired plants

Family Applications Before (1)

Application Number Title Priority Date Filing Date
US46346A Expired - Lifetime US3177249A (en) 1959-08-21 1960-08-01 N-trifluoromethylphenyl urea

Country Status (5)

Country Link
US (2) US3177249A (en)
BE (1) BE594228A (en)
DE (1) DE1302707C2 (en)
GB (2) GB899718A (en)
NL (3) NL255528A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4065292A (en) * 1975-09-24 1977-12-27 Bayer Aktiengesellschaft Herbicidal agents
US4112100A (en) * 1973-12-26 1978-09-05 The Upjohn Company Methods of use of pyridylalkyl phenylthioureas
US4137068A (en) * 1975-03-26 1979-01-30 Roussel Uclaf Novel ureas

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL129423C (en) * 1964-03-26
US3419664A (en) * 1964-03-26 1968-12-31 Geigy Chem Corp Compositions and methods for treating pain with substituted ureas
US4190431A (en) * 1966-03-18 1980-02-26 Velsicol Chemical Corporation Substituted oxadiazolidine-3,5-diones
DE1300106B (en) * 1966-07-22 1969-07-31 Hoechst Ag Process for the preparation of difluorochloromethylphenylureas
US3895061A (en) * 1968-07-17 1975-07-15 Velsicol Chemical Corp Trifluoromethyl ureas
DE2411320A1 (en) * 1974-03-09 1975-09-18 Bayer Ag (TRIFLUOROMETHYLPHENOXY) PHENYLURA, METHOD OF MANUFACTURING AND USING THEM AS HERBICIDES
IT1137177B (en) * 1981-06-02 1986-09-03 Anic Spa PROCESS FOR THE PREPARATION OF ASYMMETRICAL UREAS STARTING FROM URETANS AND AMINES
FR2577221B1 (en) * 1985-02-11 1987-02-20 Rhone Poulenc Agrochimie PROCESS FOR THE PREPARATION OF A SUBSTITUTED PHENYLUREA

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2655447A (en) * 1952-02-14 1953-10-13 Du Pont Composition and method

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2726150A (en) * 1952-10-03 1955-12-06 Du Pont Herbicidal composition and method of making same
US2723192A (en) * 1954-02-23 1955-11-08 Du Pont Herbicidal process and product

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2655447A (en) * 1952-02-14 1953-10-13 Du Pont Composition and method

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4112100A (en) * 1973-12-26 1978-09-05 The Upjohn Company Methods of use of pyridylalkyl phenylthioureas
US4137068A (en) * 1975-03-26 1979-01-30 Roussel Uclaf Novel ureas
US4065292A (en) * 1975-09-24 1977-12-27 Bayer Aktiengesellschaft Herbicidal agents

Also Published As

Publication number Publication date
BE594228A (en)
DE1302707C2 (en) 1974-04-04
GB914794A (en) 1963-01-02
NL255093A (en)
US3177249A (en) 1965-04-06
NL128363C (en)
DE1302707B (en) 1973-09-13
NL255528A (en)
GB899718A (en) 1962-06-27

Similar Documents

Publication Publication Date Title
US3223721A (en) 1-(4-bromophenyl), 3-methoxy, 3-methyl-urea
US3060235A (en) Phenyl ether-ureas
US3151023A (en) Preparations for combating phytopathogenic microorganisms
US3119682A (en) Herbicidal composition containing as the active ingredient a phenyl ether urea
US3236624A (en) Method for selectively killing undesired plants
US3429688A (en) Method for combating undesired plant growth
US3134665A (en) Method for destroying weeds
US3917478A (en) Herbicidal compositions and methods utilizing thiadiazolis ureas
US3184301A (en) Method for destroying weeds
US3454591A (en) Herbicidal 3-methyl-5-ureidoisothiazoles
DE1670924B2 (en) 1,2,4-THIADIAZOLYL UREA DERIVATIVES
US2764478A (en) Weed control composition and method
US3276855A (en) N-alkylmercapto-ureas and a method for controlling weeds
US3241942A (en) Method for combating weeds
US3823006A (en) Method for selective weed control in beets
US2923614A (en) Triazine derivatives
US3287100A (en) Method for controlling undesired plant growth
US3929816A (en) Herbicidal thiadiazolyl-ureas
US3819357A (en) Quaternary thenyl ammonium salts as plant growth control agents
US3742007A (en) N-alkyl-n-bi-, tri- or tetracycloalkyl thiocarbamates
US3078154A (en) Method for inhibiting the growth of plants
US4128412A (en) Herbicidal composition and method using N-(2-ethylsulfonyl-1,3,4-thiadiazol-5-yl)-N-methyl-N&#39;-methyl urea
US3810988A (en) Control of phytopathogenic fungi with n-benzothiazae-2-yl n-{40 {11 propylure
US3538156A (en) Cinnamamides
US3813436A (en) Phenylurea derivatives and process for their manufacture